This invention relates to sulfonylurea herbicides which control the growth of undesired vegetation and are safe to cotton or soybean plants that contain at least one gene that confers resistance to inhibitors of acetolactate synthase, agriculturally suitable compositions thereof and a method of their use.
New compounds effective for controlling the growth of undesired vegetation are in constant demand not only for the control of all plant growth but also for controlling said growth while not injuring useful crops.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last several years which generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteraromatic rings.
U.S. Pat. No. 4,723,990 discloses compounds of the formula ##STR1## wherein: L is, among others, Cl, F, Br;
R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; PA0 R.sub.1 is H, F, Cl or C.sub.1 -C.sub.4 alkyl; PA0 R.sub.2 is H or CH.sub.3 ; PA0 R.sub.8 is H, CH.sub.3 or OCH.sub.3 ; PA0 A is, among others, ##STR2## W is O or S; X is H, Cl, Br, CH.sub.3, CH.sub.2 CH.sub.3, C.sub.1 -C.sub.3 alkoxy, CF.sub.3, SCH.sub.3 or CH.sub.2 OCH.sub.3 ; PA0 Y is CH.sub.3 or OCH.sub.3 ; and PA0 Z is N, CH, CCl, CBr, CCN, CCH.sub.3, CCH.sub.2 CH.sub.3, CCH.sub.2 CH.sub.2 Cl or CCH.sub.2 CH.dbd.CH.sub.2 ; PA0 (1) when R.sub.1 is Cl, then L is Cl or Br and R.sub.2 is H; PA0 (2) when R.sub.3 is OCH.sub.3, then R.sub.4 is CH.sub.3 ; PA0 (3) when W is S, then R.sub.8 is H; and PA0 (4) when L is F, then R.sub.1 is H, F, or C.sub.1 -C.sub.4 alkyl. PA0 R.sup.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, --CO--R.sup.6, --NR.sup.7 R.sup.8, --CO--NR.sup.9 R.sup.10 or --SO.sub.2 --NR.sup.11 R.sup.12 ; PA0 R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl; PA0 R.sup.3 and R.sup.4 independently of one another are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.1 -C.sub.4 alkoxy or --NR.sup.12 R.sup.13 ; PA0 R.sup.5 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; PA0 R.sup.6 is C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.6 alkoxyalkoxy, hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl; PA0 R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12 and R.sup.13 independently of one another are each hydrogen or C.sub.1 -C.sub.4 alkyl; PA0 E is nitrogen or the methine bridge; and PA0 Z is oxygen or sulfur; PA0 R is among others, C.sub.1 -C.sub.12 alkyl; PA0 R.sub.2 is H, Cl, Br, F, C.sub.1 -C.sub.3 alkyl, --NO.sub.2, --SO.sub.2 CH.sub.3, --OCH.sub.3, --SCH.sub.3, --CF.sub.3, --N(CH.sub.3).sub.2, --NH.sub.2, or --CN; and PA0 R.sub.3 is H, Cl, Br, F or CH.sub.3. PA0 X is an unsubstituted or substituted phenyl or naphthyl radical; PA0 Y is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.2 -C.sub.3 alkoxyalkyl, halogen or an unsubstituted amino group; and PA0 Z is oxygen or sulfur. PA0 2-chloro-6-(1-fluoroethyl)-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amin o]carbonyl]benzenesulfonamide, PA0 1-methylethyl 3-chloro-2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]-carbonyl]amino]sulfonyl] benzoate, and PA0 methyl 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]-amino]sulfon yl]benzoate.
and their agriculturally suitable salts; provided that:
SA 84/2245 discloses compounds of the formula ##STR3## wherein: A is C.sub.1 -C.sub.6 haloalkyl;
and the invention relates also to the salts of these compounds, with the proviso that A is not trifluoromethyl or the group --CR.sup.a R.sup.b R.sup.c, where R.sup.a is hydrogen, chlorine or C.sub.1 -C.sub.4 alkyl, R.sup.b is hydrogen or methyl, and R.sup.c is chlorine or bromine.
U.S. Pat. No. 4,394,506 and U.S. Pat. No. 4,592,978 disclose compounds of the formula ##STR4## wherein: Q is, among other, O;
U.S. Pat. No. 4,478,635 discloses compounds of the formula ##STR5## wherein: R.sub.18 is hydrogen, alkyl or alkoxy;
None of the compounds of the instant invention are specifically disclosed in any of the above references nor do the references teach the possible use of these compounds on herbicide-resistant crops. However, compounds of the present invention are within the generic scope of the claims of the above patents.
EP-A-154,204 discloses plants, plant tissues and plant seeds, particularly corn (Zea mays L.), which are resistant to herbicides (including sulfonylureas) which normally inhibit the growth and development of those plants, plant tissues and plant seeds.
Sebastian et al. (Crop Science 1989 29:1403-1408) describe the selection, characterization and utility of soybean mutants which are resistant to sulfonylurea herbicides. Line W20 is specifically described.
EP-A-257,993 describes nucleic acid fragments useful in the production of transgenic plants on which the compounds and methods of the instant invention are used.